GB633735A - Improvements in or relating to the production of methine dyestuffs and to photographic emulsions sensitised therewith - Google Patents
Improvements in or relating to the production of methine dyestuffs and to photographic emulsions sensitised therewithInfo
- Publication number
- GB633735A GB633735A GB15448/47A GB1544847A GB633735A GB 633735 A GB633735 A GB 633735A GB 15448/47 A GB15448/47 A GB 15448/47A GB 1544847 A GB1544847 A GB 1544847A GB 633735 A GB633735 A GB 633735A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxazolone
- phenyl
- ethylidene
- dihydroquinolylidene
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title abstract 2
- 239000000839 emulsion Substances 0.000 title 1
- -1 heterocyclic nitrogen compound Chemical class 0.000 abstract 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical compound C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 abstract 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract 1
- MVVFUAACPKXXKJ-UHFFFAOYSA-N 4,5-dihydro-1,3-selenazole Chemical compound C1CN=C[Se]1 MVVFUAACPKXXKJ-UHFFFAOYSA-N 0.000 abstract 1
- SJHPCNCNNSSLPL-UHFFFAOYSA-N 4-(ethoxymethylene)-2-phenyloxazol-5-one Chemical compound O1C(=O)C(=COCC)N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- YDQJXVYGARVLRT-UHFFFAOYSA-N Lepidine Natural products C=1C=CC(CC=2NC=CN=2)=CC=1OC=1C(OC)=CC=CC=1CC1=NC=CN1 YDQJXVYGARVLRT-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Methine dyes are prepared by reacting a compound of the general formula <FORM:0633735/IV (c)/1> wherein R is alkyl, R1 is aryl, and R2 is H or alkyl, with a heterocyclic nitrogen compound containing a reactive methylene group, e.g. a compound of the general formula (A) <FORM:0633735/IV (c)/2> wherein D1 is the residue of a 5- or 6-membered heterocyclic N nucleus, R3 is alkyl, aralkyl, hydroxyalkyl, or hydroxyaralkyl, R4 is H or a hydrocarbon group, n is 0 or 1, and Y is an acid radical, or a compound of the general formula (B) <FORM:0633735/IV (c)/3> wherein Q is O or S and R5 is H or a hydrocarbon group. The compound of the general formula (A) may be derived from a thiazole, oxazole, selenazole, or a polycyclic homologue thereof (e.g. of the benzene, naphthalene, acenaphthene, or anthracene series), pyridine, quinoline, a or b -naphthoquinoline, lepidine, indolenine, a diazine (e.g. a pyrimidine or quinazoline), a diazole (e.g. thio-b : b 1-diazole), a thiazoline, oxazoline, or selenazoline, in which carbocyclic rings, if present, may be substituted with one or more alkyl, aryl, amino, hydroxy, alkoxy, or methylenedioxy groups or halogen atoms. The reagents may be heated together in presence of a solvent and a base. 3 - Ethyldihydrobenzthiazolylidene - 2 - (41-ethylidene - 21 - phenyl - 51 - oxazolone) is prepared by refluxing together 2-methylbenzthiazole etho-p-toluenesulphonate, 4-ethoxymethylene - 2 - phenyl - 5 - oxazolone, and pyridine. 3 - Ethyldihydrobenzthiazolylidene-2 - (41 - isopropylidene - 21 - phenyl - 51 - oxazolone), 3 - ethyldihydrobenzthiazolylidene - 2-(41 - isobutylidene - 21 - phenyl - 51 - oxazolone), 1 : 3 : 3 - trimethylindolylidene - 2 - (41 - ethylidene - 21 - phenyl - 51 - oxazolone), 1 - ethyl1 : 2 - dihydroquinolylidene - 2 - (41 - ethylidene-21 - phenyl - 51 - oxazolone), 1 - ethyl - 1 : 2 - dihydroquinolylidene - 2 - (41 - isopropylidene - 21-phenyl - 51 - oxazolone), 1 - ethyl - 1 : 4 - dihydroquinolylidene - 4 - (41 - ethylidene - 21-phenyl - 51 - oxazolone), 1 - methyl - 1 : 4-dihydroquinolylidene - 4 - (41 - ethylidene - 21-phenyl - 51 - oxazolone), 3 - ethyldihydrobenzselenazolylidene - 2 - (41 - ethylidene - 21 - phenyl-51 - oxazolone), 3 : 4 - dimethyldihydrothiazolylidene - 2 - (41 - ethylidene - 21 - phenyl - 51-oxazolone), 3 - ethyldihydrobenzoxazolylidene - 2-(41 - ethylidene - 21 - phenyl - 51 - oxazolone) 3 - methyltetrahydrothiazolylidene - 2 - (41-ethylidene - 21 - phenyl - 51 - oxazolone), 3-methyltetrahydrothiazolylidene - 2 - (41 - isopropylidene - 21 - phenyl - 51 - oxazolone), 4 - keto2 - thiotetrahydrothiazole - 5 - (41 - methylene21 - phenyl - 51 - oxazolone), 3 - ethyl - 2 : 3-dihydrobenzoxazolylidene - 2 - (41 - propylidene21 - phenyl - 51 - oxazolone), 3 - ethyl - 2 : 3-dihydrobenzoxazolylidene - 2 - (41 - isobutylidene21 - phenyl - 51 - oxazolone), 3 - methyltetrahydrothiazolylidene - 2 - (41 - isobutylidene - 21-phenyl - 51 - oxazolone), 1 - methyl - 1 : 4-dihydroquinolylidene - 4 - (41 - propylidene - 21-phenyl - 51 - oxazolone), and 1 - ethyl - 1 : 2-dihydroquinolylidene - 2 - (41 - isobutylidene - 21-phenyl-51-oxazolone) are similarly prepared. Specifications 549,202, 585,089 and 633,736, [Group IV (b)], are referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15448/47A GB633735A (en) | 1947-06-11 | 1947-06-11 | Improvements in or relating to the production of methine dyestuffs and to photographic emulsions sensitised therewith |
| US30974A US2556545A (en) | 1947-06-11 | 1948-06-03 | Production of methine dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15448/47A GB633735A (en) | 1947-06-11 | 1947-06-11 | Improvements in or relating to the production of methine dyestuffs and to photographic emulsions sensitised therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB633735A true GB633735A (en) | 1949-12-19 |
Family
ID=10059319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15448/47A Expired GB633735A (en) | 1947-06-11 | 1947-06-11 | Improvements in or relating to the production of methine dyestuffs and to photographic emulsions sensitised therewith |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2556545A (en) |
| GB (1) | GB633735A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE522770A (en) * | 1952-09-15 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2185343A (en) * | 1940-01-02 | Polymethine dyes and process for | ||
| US2353164A (en) * | 1944-07-11 | Dyestuffs and dyestuff | ||
| FR810104A (en) * | 1935-08-16 | 1937-03-15 | Ilford Ltd | Improvements to dyeing materials |
| US2342546A (en) * | 1936-11-14 | 1944-02-22 | Ilford Ltd | Production and use of dyestuffs |
| US2166736A (en) * | 1937-04-23 | 1939-07-18 | Eastman Kodak Co | Photographic emulsion |
| DE873357C (en) * | 1937-04-23 | 1953-04-13 | Kodak Ag | Process for sensitizing halogen silver emulsions |
| US2263757A (en) * | 1937-12-16 | 1941-11-25 | Eastman Kodak Co | Ketone dye and process for preparing it |
| US2226158A (en) * | 1939-05-09 | 1940-12-24 | Eastman Kodak Co | Photographic emulsion |
| GB534140A (en) * | 1939-05-25 | 1941-02-28 | Kodak Ltd | Improvements in and relating to photographic emulsions and layers, and the manufacture of dyes for use therein and intermediates for such manufacture |
| US2369555A (en) * | 1941-10-08 | 1945-02-13 | Freeman Harry Howard | Tool-adjusting means |
-
1947
- 1947-06-11 GB GB15448/47A patent/GB633735A/en not_active Expired
-
1948
- 1948-06-03 US US30974A patent/US2556545A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US2556545A (en) | 1951-06-12 |
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